WO2001018131A1 - Method for producing a wood coating agent - Google Patents

Method for producing a wood coating agent Download PDF

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Publication number
WO2001018131A1
WO2001018131A1 PCT/DE2000/003096 DE0003096W WO0118131A1 WO 2001018131 A1 WO2001018131 A1 WO 2001018131A1 DE 0003096 W DE0003096 W DE 0003096W WO 0118131 A1 WO0118131 A1 WO 0118131A1
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WO
WIPO (PCT)
Prior art keywords
light
wood
laser dye
binder
coating
Prior art date
Application number
PCT/DE2000/003096
Other languages
German (de)
French (fr)
Inventor
Stefan Friebel
Rudi Danz
Original Assignee
Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. filed Critical Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V.
Priority to AU75073/00A priority Critical patent/AU7507300A/en
Priority to EP00963978A priority patent/EP1228152A1/en
Publication of WO2001018131A1 publication Critical patent/WO2001018131A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • C09D175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
    • B05D7/06—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials to wood
    • B05D7/08—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials to wood using synthetic lacquers or varnishes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
    • B05D3/06—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation
    • B05D3/061—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation using U.V.
    • B05D3/065—After-treatment
    • B05D3/067—Curing or cross-linking the coating

Definitions

  • the invention relates to a method for producing a transparent coating agent for the coating of wood with special etter and light-protecting properties.
  • Field of application is the coating of wooden facades, windows, doors, wooden cladding and the like.
  • glazing or colorless coatings are used to protect wood, high-energy radiation from the sun spectrum leads to degradation reactions in the paint film. But also the lignin in the underlying wooden surface is destroyed and in combination with moisture leads to the removal of the colorless lacquer film.
  • US Pat. No. 5,338,613 describes photopolymerizable polyurethane acrylates for weather-resistant coatings.
  • Organic UV absorbers and pigments are added to the paint to stabilize the light.
  • the organic UV absorbers absorb the photonic energy, they have the disadvantage that their effectiveness decreases over time and thus pass on the absorbed light energy to the lattice of the polymer binder and in this way leads to a light-induced degradation of the polymer in the long term.
  • paint formulations containing pigments are less suitable for wood coatings, because on the one hand they hide the wood grain and on the other hand they tend to flake off after being used for more than 5 years.
  • UV shielding Another protective measure against damaging UV radiation is UV shielding.
  • the principle of action of this method is the complete shielding of UV radiation by adding UV-absorbing iron oxide pigments.
  • these iron oxide pigments have the decisive disadvantage of coloring and covering properties, so that they are not suitable for producing colorless coatings.
  • coatings containing iron oxide are difficult to crosslink with UV light. As already mentioned, they also tend to peel off the paint film and chalk out the pigment after only a few years.
  • the invention has for its object to provide a manufacturing method for a largely weather and UV stable wood coating agent.
  • a method for producing a transparent coating agent for the coating of wood in which a binder is selected from the group consisting of the physically drying acrylic resins or radiation-curing acrylic resins and then doped with at least one highly efficient and light-stable laser dye, which is in the form of 0.1 - 5.0% by weight, based on the total composition, is dissolved in the binder in a molecularly disperse manner and the UV component of the UV light and spectral light components in the wavelength range between 280 nm and 500 nm are absorbed completely or selectively and with a conversion efficiency of> 30% in converts undulating radiation which does not damage the wood substrates and the binder, at least one photoinitiator, auxiliary substances and optionally solvents being added.
  • methylbenzoylforma Irgacure 184, Irgacure 819 or P37 (benzophenone derivative) are used as the photoinitiator, alone or in combination, other photoinitiators also being conceivable.
  • UV-curing polyurethane acrylates can be used as the acrylate resins.
  • An alternative solution according to the invention based on another binder is a process for producing a transparent coating agent for the coating of wood, in which a binder is selected from the group of medium to long oil alkyd resins based on drying fatty acids and / or drying oils and then with at least a highly efficient and light-stable laser dye is doped, which is dissolved in the form of 0.1 - 5.0% by weight based on the total composition in the binder in a molecularly disperse manner and the UV component of the UV light and spectral light components in the wavelength range between 280 nm and 500 nm completely or selectively absorbed and with a conversion efficiency of>. 30% is converted into longer-wave radiation that does not damage the wood substrates and the binding agent, with additives and possibly solvents being added.
  • the coating according to the invention also provides high light protection in the blue spectral range and is light-stable.
  • the coating systems according to the invention can be crosslinked using the economical technology of radiation curing (for example by means of UV radiation).
  • the coatings are transparent so that the wood grain can take full effect and is not covered by pigments.
  • the production technology of the layers is economically efficient and easy to implement.
  • the layer thickness of the paint to be coordinated with the concentration of the respective laser dye.
  • the at least one laser dye is to be matched to the intended use and is selected from special rhodamines, pyrro ethenes, exalites, furan or lumogens.
  • rhodamines rhodamine 560, rhodamine 575, rhodamine 590 and rhodamine 610 are particularly suitable.
  • Particularly suitable pyrromethenes are pyrromethene 546, pyrromethene 556, pyrroethene 567, pyrromethene 580, pyrromethene 597 and 1,4-di [2- (5-phenyloxazolyl)] benzene.
  • Exalit 428, Exalit 400E, Exalit 404, Exalit 411, Exalit 417, LD466, LD473 and LD489 have proven to be particularly suitable.
  • Preferred Lumogens are Lumogen F240, Lumogen F Red 300, Lumogen F Violet 570 and Lumogen F Yellow 083.
  • one or more laser dyes can be used in combination with an organic UV absorber.
  • Flow additives, wetting additives or the like can be considered as auxiliary substances. Fillers can also be added to reduce the price of the coating agent.
  • the coating system has a high viscosity, the addition of a solvent, e.g. Acetone, required.
  • a solvent e.g. Acetone
  • 0.04 g Lumogen F Violett 570 are dissolved in 4 g hexanediol diacrylate and 1 g Ebecryl 112 and then mixed with 5 g IRR 245.
  • 0.3 g Tinuvin 400, 0.05 g BYK 333, 0.04 g BYK 088 and 0.3 g P37 (benzophenone derivative - photoinitiator) are added to this mixture.
  • the lacquer film is cross-linked with UV radiation (mercury (Hg) or gallium (Ga) -doped Hg lamp).
  • the crosslinking can take place under a normal atmosphere or better under an inert gas (eg nitrogen).
  • Embodiment 2 Embodiment 2
  • 0.05 Lumogen F Violett 570 is dissolved in 4 g of hexanediol diacrylate and 1 g of Ebecryl 111 and then mixed with 2 g of Ebecryl 284 and 3 g of IRR 245.
  • 0.2 g Tinuvin 400, 0.04 g BYK 333, 0.04 g BYK 088 and 0.3 g P37 (benzophenone derivative - photoinitiator) are added to this mixture.
  • the lacquer film is cross-linked with UV radiation (Hg or Ga-doped Hg lamp). The crosslinking can take place under a normal atmosphere or better under an inert gas (e.g. nitrogen).
  • Lumogen F Violett 570 is dissolved in 3 g of hexanediol diacrylate, 1 g of Ebecryl 112 and 1 g of acetone and then mixed with 2 g of Ebecryl 284 and 4 g of IRR 245. 0.04 g BYK 333, 0.04 g BYK 088 and 0.3 g P37 (benzophenone derivative - photoinitiator) are added to this mixture. After application to the wood, the lacquer film is cross-linked with UV radiation (Hg or Ga-doped Hg lamp). The crosslinking can take place under a normal atmosphere or better under an inert gas (e.g. nitrogen).
  • an inert gas e.g. nitrogen
  • the laser dyes Lumogen F Red 300 and / or F Violet 570 are dissolved in xylene (300 mg each in 20 ml xylene). 1.33 g of the laser dye solution are then added to the mixture of 2.0 g Ebecryl and 0.90 g HDDA with the addition of the photoinitiator methylbenzoyl format (3%). The laser dye lacquer formulation is cured on wooden substrates with UV radiation.
  • Ebecryl 111, Ebecryl 112, Ebecryl 284, IRR 245 and P37 are trademarks of UCB Chemicals.
  • BYK 333, BYK 088 are trademarks of BYK Chemie GmbH.
  • Tinuvin 400 is a trademark of Ciba Specialty Chemicals.
  • Lumogen is a trademark of BASF AG for fluorescent pigments based on aldazine derivatives.
  • Primal is a trademark of Röhm and Haas.
  • Mobilcer is a trademark of Mobil Corp.
  • Furan is a trademark of Lambda Physik GmbH for benzofurans, especially bis (benzo [b] furan-2-yl) biphenyls, especially benzofuran 2, 2 '- [1, 1' -biphenyl] -4, 4 '-diyl-bis - tetrasulfonic acid (tetrasodium salt), sold under the Lambdachrome ' 1 ' No. 4260.
  • Rhodamine 560 o- (6-amino-3-imino-3H-xanthene-9-yl) -benzoic acid Rhodamine 575
  • Ebecryl 112 aliphatic monoacrylate Ebecryl 284 difunctional aliphatic polyurethane acrylate (molecular weight 1200 g / mol) IRR 245 difunctional aliphatic polyurethane acrylate (molecular weight 6100 g / mol) P37 oligo eres benzophenone

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Paints Or Removers (AREA)
  • Chemical And Physical Treatments For Wood And The Like (AREA)

Abstract

The invention relates to a method for producing a transparent coating agent for coating wood. According to the invention, a binding agent is selected from the group of physically drying acrylate resins or from acrylate resins that are cross-linked by irradiation, and is subsequently doped with at least one highly efficient and light-stable laser dye. Said laser dye, in the amount of 0.1 to 5.0 wt. % with regard to the entire composition, is dissolved in the binding agent molecule in a dispersed manner. The UV portion of the UV light as well as spectral light portions with wavelengths ranging from 280 nm to 500 nm are completely or selectively absorbed and, with a conversion efficiency of >/= 30 %, are converted into longer wave radiation that does not damage the wood substrates nor the binding agent, whereby at least one photoinitiator, auxiliary agents and, optionally, solvents are admixed.

Description

Verfahren zur Herstellung eines Holzbeschichtungs ittelsProcess for producing a wood coating material
Die Erfindung betrifft ein Verfahren zur Herstellung eines transparenten Überzugsmittels für die Beschichtung von Holz mit speziellen etter- und lichtschützenden Eigenschaften. Anwendungsgebiet ist die Beschichtung von Holzfassaden, Fenstern, Türen, Holzverkleidungen und dergleichen.The invention relates to a method for producing a transparent coating agent for the coating of wood with special etter and light-protecting properties. Field of application is the coating of wooden facades, windows, doors, wooden cladding and the like.
Werden zum Schutz von Holz lasierende oder farblose Beschichtun- gen angewendet, führt energiereiche Strahlung aus dem Sonnenspektrum zu Abbaureaktionen im Lackfilm. Aber auch das Lignin in der darunterliegenden Holzoberfläche wird zerstört und führt in Kombination mit Feuchte zum Ablösen des farblosen Lackfilmes.If glazing or colorless coatings are used to protect wood, high-energy radiation from the sun spectrum leads to degradation reactions in the paint film. But also the lignin in the underlying wooden surface is destroyed and in combination with moisture leads to the removal of the colorless lacquer film.
In der Patentschrift US 5,338,613 werden photopolymerisierbare Polyurethanacrylate für wetterbeständige Beschichtungen beschrieben. Zur Lichtstabilisierung werden dem Lack organische UV-Absorber und Pigmente zugegeben. Die organischen UV-Absorber absorbieren zwar die photonische Energie, sie haben aber den Nachteil, dass ihre Wirksamkeit im Laufe der Zeit abnimmt und somit die absorbierte Lichtenergie an das Gitter des Polymerbinders weitergeben und auf diese Weise langfristig zu einem lichtinduzierten Abbau des Polymers führt. Weiterhin sind Pigmente enthaltende Lackformulierungen für Holzanstriche weniger gut geeignet, da sie zum einen die Holzmaserung verdecken und zum anderen nach einer Anwendung länger als 5 Jahre zum Abblättern neigen.US Pat. No. 5,338,613 describes photopolymerizable polyurethane acrylates for weather-resistant coatings. Organic UV absorbers and pigments are added to the paint to stabilize the light. Although the organic UV absorbers absorb the photonic energy, they have the disadvantage that their effectiveness decreases over time and thus pass on the absorbed light energy to the lattice of the polymer binder and in this way leads to a light-induced degradation of the polymer in the long term. Furthermore, paint formulations containing pigments are less suitable for wood coatings, because on the one hand they hide the wood grain and on the other hand they tend to flake off after being used for more than 5 years.
In der US 5,840,788 sind Urethan-Beschichtungen für Golfbälle beansprucht. Die dabei verwendeten Aufheller sind nicht lang- zeitphotostabil . Ihre Strahlungsumwandlungseffizienz ist nicht ausreichend. Diese Beschichtungen sind für einen ausreichenden Holzschutz ebenfalls nicht geeignet. Insbesondere beachten die bisherigen erfinderischen Lösungen nicht, dass Holz auch durch Strahlung im blauen Spektralbereich abgebaut wird. Als eine Alternative werden nano-Metalloxide in der Patentschrift 5,817,160 beschrieben, wie z.B. Ti02, die die Eigenschaften besitzen, UV-Licht zu absorbieren, im sichtbaren Licht jedoch transparent zu sein. Diese Technik des UV-Schutzes hat den Vorteil, dass sich die nano-Metalloxide im Gegensatz zu den organischen UV-Absorbern nicht verbrauchen. Der Nachteil hier bei Klarlacken ist der unzureichende Schutz von UV-Licht des Spektralbereichs von 400 bis 440 nm , was nur einen unzureichenden Schutz für das Holz gewährt.In US 5,840,788 urethane coatings for golf balls are claimed. The brighteners used are not long-term photo-stable. Your radiation conversion efficiency is not sufficient. These coatings are also unsuitable for adequate wood protection. In particular, the previous inventive solutions do not take into account that wood is also broken down by radiation in the blue spectral range. As an alternative, nano-metal oxides are described in the patent 5,817,160, such as Ti0 2 , which have the properties of absorbing UV light but being transparent in visible light. This technique of UV protection has the advantage that, unlike organic UV absorbers, the nano-metal oxides are not consumed. The disadvantage here with clear lacquers is the inadequate protection of UV light in the spectral range from 400 to 440 nm, which only provides inadequate protection for the wood.
Eine andere Schutzmaßnahme gegen die schädigende UV-Strahlung ist die UV-Abschirmung. Das Wirkprinzip dieser Methode ist die komplette Abschirmung der UV-Strahlung durch Zusatz von UV-ab- sorbierenden Eisenoxidpigmenten. Diese Eisenoxidpigmente weisen aber den entscheidenden Nachteil von farbgebenden und deckenden Eigenschaften auf, sodass sie zur Herstellung farbloser Überzüge nicht geeignet sind. Im Gegensatz zu den UV-Absorbern und Lichtschutzmitteln lassen sich Überzüge, die Eisenoxid enthalten, nur schwer mit UV-Licht vernetzen. Sie neigen außerdem, wie schon erwähnt, nach nur wenigen Jahren zum Abblättern des Lackfilms und Auskreiden des Pigmentes .Another protective measure against damaging UV radiation is UV shielding. The principle of action of this method is the complete shielding of UV radiation by adding UV-absorbing iron oxide pigments. However, these iron oxide pigments have the decisive disadvantage of coloring and covering properties, so that they are not suitable for producing colorless coatings. In contrast to UV absorbers and light stabilizers, coatings containing iron oxide are difficult to crosslink with UV light. As already mentioned, they also tend to peel off the paint film and chalk out the pigment after only a few years.
Der Erfindung liegt die Aufgabe zugrunde, ein Herstellungsverfahren für ein weitgehend witterungs- und UV-stabiles Holz-Über- zugsmittel zur Verfügung zu stellen.The invention has for its object to provide a manufacturing method for a largely weather and UV stable wood coating agent.
Diese Aufgabe wird erfindungsgemäß gelöst durch ein Verfahren zur Herstellung eines transparenten Überzugsmittels für die Beschichtung von Holz, bei dem ein Bindemittel aus der Gruppe der physikalisch trocknenden Acrylatharze oder strahlenvernetzenden Acrylatharze ausgewählt und dann mit zumindest einem hocheffizienten und lichtstabilen Laserfarbstoff dotiert wird, der in Form von 0,1 - 5,0 Gew.-% bezogen auf die Gesamtzusammensetzung in dem Bindemittel molekular dispers gelöst wird und den UV-An- teil des UV-Lichtes sowie spektrale Lichtanteile im Wellenlängenbereich zwischen 280 nm und 500 nm vollständig oder selektiv absorbiert und mit einer Konversionseffizienz von > 30% in län- gerwellige, die Holzsubstrate und das Bindemittel nicht schädigende Strahlung umwandelt, wobei zumindest ein Photoinitiator, Hilfsstoffe und gegebenenfalls Lösemittel beigemischt werden.This object is achieved according to the invention by a method for producing a transparent coating agent for the coating of wood, in which a binder is selected from the group consisting of the physically drying acrylic resins or radiation-curing acrylic resins and then doped with at least one highly efficient and light-stable laser dye, which is in the form of 0.1 - 5.0% by weight, based on the total composition, is dissolved in the binder in a molecularly disperse manner and the UV component of the UV light and spectral light components in the wavelength range between 280 nm and 500 nm are absorbed completely or selectively and with a conversion efficiency of> 30% in converts undulating radiation which does not damage the wood substrates and the binder, at least one photoinitiator, auxiliary substances and optionally solvents being added.
Erfindungsgemäß ist es zweckmäßig, wenn als Photoinitiator Me- thylbenzoylforma , Irgacure 184, Irgacure 819 oder P37 (Benzo- phenonderivat ) allein oder in Kombination eingesetzt werden, wobei auch andere Photoinitiatoren denkbar sind. Dabei können als Acrylatharze UV-vernetzende Polyurethanacrylate verwendet werden.According to the invention, it is expedient if methylbenzoylforma, Irgacure 184, Irgacure 819 or P37 (benzophenone derivative) are used as the photoinitiator, alone or in combination, other photoinitiators also being conceivable. UV-curing polyurethane acrylates can be used as the acrylate resins.
Eine auf einem anderen Bindemittel basierende erfindungsgemäße Alternativlösung ist ein Verfahren zur Herstellung eines transparenten Überzugsmittels für die Beschichtung von Holz, bei dem ein Bindemittel aus der Gruppe mittel- bis langöliger Alkydhar- ze auf Basis trocknender Fettsäuren und/oder trocknender Öle ausgewählt und dann mit zumindest einem hocheffizienten und lichtstabilen Laserfarbstoff dotiert wird, der in Form von 0,1 - 5,0 Gew.-% bezogen auf die Gesamtzusammensetzung in dem Binde- mittel molekular dispers gelöst wird und den UV-Anteil des UV- Lichtes sowie spektrale Lichtanteile im Wellenlängenbereich zwischen 280 nm und 500 nm vollständig oder selektiv absorbiert und mit einer Konversionseffizienz von >. 30 % in längerwellige, die Holzsubstrate und das Bindemittel nicht schädigende Strahlung umwandelt, wobei Hilfsstoffe und gegebenenf lls Lösemittel beigemischt werden.An alternative solution according to the invention based on another binder is a process for producing a transparent coating agent for the coating of wood, in which a binder is selected from the group of medium to long oil alkyd resins based on drying fatty acids and / or drying oils and then with at least a highly efficient and light-stable laser dye is doped, which is dissolved in the form of 0.1 - 5.0% by weight based on the total composition in the binder in a molecularly disperse manner and the UV component of the UV light and spectral light components in the wavelength range between 280 nm and 500 nm completely or selectively absorbed and with a conversion efficiency of>. 30% is converted into longer-wave radiation that does not damage the wood substrates and the binding agent, with additives and possibly solvents being added.
Die erfindungsgemäße Beschichtung übt gegenüber dem Holzsubstrat auch im blauen Spektralbereich einen hohen Lichtschutz aus und ist lichtstabil. Die erfindungsgemäßen Beschichtungssysteme können durch die wirtschaftliche Technik der Strahlenhärtung (z.B. durch UV-Strahlung) vernetzt werden. Darüberhinaus sind die Beschichtungen transparent, sodass die Holzmaserung voll zur Wirkung kommen kann und nicht durch Pigmente verdeckt wird. Die Herstellungstechnologie der Schichten ist ökonomisch effizient und leicht umsetzbar. Dabei ist die Schichtdicke des Anstrichs mit der Konzentration des jeweiligen Laserfarbstoffs abzustimmen.Compared to the wooden substrate, the coating according to the invention also provides high light protection in the blue spectral range and is light-stable. The coating systems according to the invention can be crosslinked using the economical technology of radiation curing (for example by means of UV radiation). In addition, the coatings are transparent so that the wood grain can take full effect and is not covered by pigments. The production technology of the layers is economically efficient and easy to implement. Here is the layer thickness of the paint to be coordinated with the concentration of the respective laser dye.
Der zumindest eine Laserfarbstoff ist auf den Anwendungszweck abzustimmen und wird aus speziellen Rhodaminen, Pyrro ethenen, Exaliten, Furan oder Lumogenen ausgewählt. Dabei kommen von den Rhodaminen insbesondere Rhodamin 560, Rhodamin 575, Rhodamin 590 und Rhodamin 610 in Frage. Als Pyrromethene eignen sich insbesondere Pyrromethen 546, Pyrromethen 556, Pyrro ethen 567, Pyr- romethen 580, Pyrromethen 597 und 1 , 4-Di[ 2- ( 5-phenyloxazolyl) ] benzen. Von den Exaliten haben sich als besonders geeignet erwiesen Exalit 428, Exalit 400E, Exalit 404, Exalit 411, Exalit 417, LD466, LD473 und LD489. Bevorzugte Lumogene sind Lumogen F240, Lumogen F Rot 300, Lumogen F Violett 570 und Lumogen F Gelb 083.The at least one laser dye is to be matched to the intended use and is selected from special rhodamines, pyrro ethenes, exalites, furan or lumogens. Of the rhodamines, rhodamine 560, rhodamine 575, rhodamine 590 and rhodamine 610 are particularly suitable. Particularly suitable pyrromethenes are pyrromethene 546, pyrromethene 556, pyrroethene 567, pyrromethene 580, pyrromethene 597 and 1,4-di [2- (5-phenyloxazolyl)] benzene. Of the Exalites, Exalit 428, Exalit 400E, Exalit 404, Exalit 411, Exalit 417, LD466, LD473 and LD489 have proven to be particularly suitable. Preferred Lumogens are Lumogen F240, Lumogen F Red 300, Lumogen F Violet 570 and Lumogen F Yellow 083.
Da nicht alle Laserfarbstoffe den gewünschten Wellenlängenbereich absorbieren, können ein oder mehrere Laserfarbstoffe in Kombination mit einem organischen UV-Absorber verwendet werden.Since not all laser dyes absorb the desired wavelength range, one or more laser dyes can be used in combination with an organic UV absorber.
Als Hilfsstoffe kommen Verlaufsadditive, Netzadditive oder dergleichen in Frage. Zur Preisreduzierung des Überzugsmittels können außerdem Füllstoffe beigegeben werden.Flow additives, wetting additives or the like can be considered as auxiliary substances. Fillers can also be added to reduce the price of the coating agent.
Bei hoher Viskosität des Lacksystems ist die Zugabe eines Lösemittels, z.B. Aceton, erforderlich.If the coating system has a high viscosity, the addition of a solvent, e.g. Acetone, required.
Ausführungsbeispiel 1Embodiment 1
0,04 g Lumogen F Violett 570 werden in 4 g Hexandioldiacrylat und 1 g Ebecryl 112 gelöst und anschließend mit 5 g IRR 245 versetzt. Diesem Gemisch werden 0,3 g Tinuvin 400, 0,05 g BYK 333, 0,04 g BYK 088 und 0,3 g P37 (Benzophenonderivat - Photoinitiator) zugegeben. Nach Applikation auf dem Holz wird der Lackfilm mit UV-Strahlung (Quecksilber (Hg) oder Gallium (Ga) -dotierte Hg-Lampe) vernetzt. Die Vernetzung kann unter Normalatmosphäre oder besser unter Inertgas (z.B. Stickstoff) stattfinden. Ausführungsbeispiel 20.04 g Lumogen F Violett 570 are dissolved in 4 g hexanediol diacrylate and 1 g Ebecryl 112 and then mixed with 5 g IRR 245. 0.3 g Tinuvin 400, 0.05 g BYK 333, 0.04 g BYK 088 and 0.3 g P37 (benzophenone derivative - photoinitiator) are added to this mixture. After application to the wood, the lacquer film is cross-linked with UV radiation (mercury (Hg) or gallium (Ga) -doped Hg lamp). The crosslinking can take place under a normal atmosphere or better under an inert gas (eg nitrogen). Embodiment 2
0,05 Lumogen F Violett 570 werden in 4 g Hexandioldiacrylat und 1 g Ebecryl 111 gelöst und anschließend mit 2 g Ebecryl 284 und 3 g IRR 245 versetzt. Diesem Gemisch werden 0,2 g Tinuvin 400, 0,04 g BYK 333, 0,04 g BYK 088 und 0,3 g P37 (Benzophenonderivat - Photoinitiator) zugegeben. Nach Applikation auf dem Holz wird der Lackfilm mit UV-Strahlung (Hg oder Ga-dotierte Hg-Lampe) vernetzt. Die Vernetzung kann unter Normalatmosphäre oder besser unter Inertgas (z.B. Stickstoff) stattfinden.0.05 Lumogen F Violett 570 is dissolved in 4 g of hexanediol diacrylate and 1 g of Ebecryl 111 and then mixed with 2 g of Ebecryl 284 and 3 g of IRR 245. 0.2 g Tinuvin 400, 0.04 g BYK 333, 0.04 g BYK 088 and 0.3 g P37 (benzophenone derivative - photoinitiator) are added to this mixture. After application to the wood, the lacquer film is cross-linked with UV radiation (Hg or Ga-doped Hg lamp). The crosslinking can take place under a normal atmosphere or better under an inert gas (e.g. nitrogen).
Ausführungsbeispiel 3Embodiment 3
0,1 g Lumogen F Violett 570 werden in 3 g Hexandioldiacrylat, l g Ebecryl 112 und 1 g Aceton gelöst und anschließend mit 2 g Ebecryl 284 und 4 g IRR 245 versetzt. Diesem Gemisch werden 0,04 g BYK 333, 0,04 g BYK 088 und 0,3 g P37 (Benzophenonderivat - Photoinitiator) zugegeben. Nach Applikation auf dem Holz wird der Lackfilm mit UV-Strahlung (Hg oder Ga-dotierte Hg-Lampe) vernetzt. Die Vernetzung kann unter Normalatmosphäre oder besser unter Inertgas (z.B. Stickstoff) stattfinden.0.1 g of Lumogen F Violett 570 is dissolved in 3 g of hexanediol diacrylate, 1 g of Ebecryl 112 and 1 g of acetone and then mixed with 2 g of Ebecryl 284 and 4 g of IRR 245. 0.04 g BYK 333, 0.04 g BYK 088 and 0.3 g P37 (benzophenone derivative - photoinitiator) are added to this mixture. After application to the wood, the lacquer film is cross-linked with UV radiation (Hg or Ga-doped Hg lamp). The crosslinking can take place under a normal atmosphere or better under an inert gas (e.g. nitrogen).
Ausführungsbeispiel 4Embodiment 4
300 mg des Laserfarbstoffes Lumogen F 240 und/oder des Laser- farbstoffes Pyrromethen 546 werden in 100 ml Dimethylformamid im Ultraschallbad gelöst und der Rückstand abgefiltert. 10 g des Filtrats wird mit 10 g Ebecryl 284, 4 g HDDA, 1 ml Aceton und 0,3 g des Photoinitiators Benzoinethylether gemischt. Der herge- stellte Lack wird auf einem Holzsubstrat aufgebracht und mit UV- Strahlung im Wellenlängenbereich von 340 bis 380 nm mit anschließender Temperaturbehandlung bei 100 °C ausgehärtet. Es entstehen lichtstabile Schichten, die im Wellenlängenbereich unterhalb 450 nm eine Absorption > 95 % aufweisen und damit einen ausreichenden Lichtschutz für Holz bieten. Ausführungsbeispiel 5300 mg of the Lumogen F 240 laser dye and / or the Pyrromethen 546 laser dye are dissolved in 100 ml of dimethylformamide in an ultrasonic bath and the residue is filtered off. 10 g of the filtrate is mixed with 10 g of Ebecryl 284, 4 g of HDDA, 1 ml of acetone and 0.3 g of the photoinitiator benzoin ethyl ether. The lacquer produced is applied to a wooden substrate and cured with UV radiation in the wavelength range from 340 to 380 nm with subsequent temperature treatment at 100 ° C. The result is light-stable layers that have an absorption> 95% in the wavelength range below 450 nm and thus offer sufficient light protection for wood. Embodiment 5
Die Laserfarbstoffe Lumogen F Rot 300 und/oder F Violett 570 werden Xylen gelöst (je 300 mg in 20 ml Xylen) . 1,33 g der La- serfarbstoff-Lösung werden dann dem Gemisch aus 2,0 g Ebecryl und 0,90 g HDDA zugegeben unter Zusatz des Photoinitiators Me- thylbenzoylformat (3 %). Die Laserfarbstoff-Lackformulierung wird auf Holzsubstraten mit UV-Strahlung ausgehärtet.The laser dyes Lumogen F Red 300 and / or F Violet 570 are dissolved in xylene (300 mg each in 20 ml xylene). 1.33 g of the laser dye solution are then added to the mixture of 2.0 g Ebecryl and 0.90 g HDDA with the addition of the photoinitiator methylbenzoyl format (3%). The laser dye lacquer formulation is cured on wooden substrates with UV radiation.
Ausführungsbeispiel 6Embodiment 6
8 g Primal E 3083 (Acrylatharz ) werden mit 0,3 g Butylglycol 0,25 g Mobilcer M, 0,01 g Ammoniak und 0,5 g Wasser dispergiert. Zu dieser Emulsion wird eine Lösung von 0,05 g Lumogen F Violett 570, 0,2 g Tinuvin 400, 0,04 g BYK 333, 0,05 g BYK 022 in 5 ml Aceton gegeben. Nach Applikation auf dem Holz vernetzt das Harz zu einem witterungsbeständigen Lackfilm.8 g of Primal E 3083 (acrylic resin) are dispersed with 0.3 g of butyl glycol, 0.25 g of Mobilcer M, 0.01 g of ammonia and 0.5 g of water. A solution of 0.05 g Lumogen F Violett 570, 0.2 g Tinuvin 400, 0.04 g BYK 333, 0.05 g BYK 022 in 5 ml acetone is added to this emulsion. After application to the wood, the resin cross-links to form a weather-resistant lacquer film.
Ebecryl 111, Ebecryl 112, Ebecryl 284, IRR 245 und P37 sind Schutzmarken von UCB Chemicals.Ebecryl 111, Ebecryl 112, Ebecryl 284, IRR 245 and P37 are trademarks of UCB Chemicals.
BYK 333, BYK 088 sind Schutzmarken von BYK Chemie GmbH. Tinuvin 400 ist eine Schutzmarke von Ciba Speciality Chemicals. Lumogen ist eine Schutzmarke der BASF AG für Fluoreszenz- Pigmente auf der Basis von Aldazin-Derivaten. Primal ist eine Schutzmarke von Röhm und Haas. Mobilcer ist eine Schutzmarke der Mobil Corp.BYK 333, BYK 088 are trademarks of BYK Chemie GmbH. Tinuvin 400 is a trademark of Ciba Specialty Chemicals. Lumogen is a trademark of BASF AG for fluorescent pigments based on aldazine derivatives. Primal is a trademark of Röhm and Haas. Mobilcer is a trademark of Mobil Corp.
Furan ist eine Schutzmarke der Lambda Physik GmbH für Benzofurane, insbesondere Bis (benzo [b] furan-2-yl ) biphenyle , insbesondere Benzofuran 2 , 2 ' - [ 1 , 1 ' -biphenyl ] -4 , 4 ' -diyl-bis- tetrasulfonsäure (Tetranatriumsalz), vertrieben unter der Lambdachrome'1' Nr. 4260.Furan is a trademark of Lambda Physik GmbH for benzofurans, especially bis (benzo [b] furan-2-yl) biphenyls, especially benzofuran 2, 2 '- [1, 1' -biphenyl] -4, 4 '-diyl-bis - tetrasulfonic acid (tetrasodium salt), sold under the Lambdachrome ' 1 ' No. 4260.
Für obige Erzeugnisse lassen sich folgende chemische Bezeichnungen angeben:The following chemical names can be given for the above products:
Rhodamin 560 o- ( 6-Amino-3-imino-3H-xanthen-9-yl ) -benzoic acid Rhodamin 575Rhodamine 560 o- (6-amino-3-imino-3H-xanthene-9-yl) -benzoic acid Rhodamine 575
Benzoic Acid, 2- [ 6- (ethylamino) -3- (ethylimino) -2 , 7-dimethyl-3H- xanthen-9-yl] ,perchlorateBenzoic acid, 2- [6- (ethylamino) -3- (ethylimino) -2, 7-dimethyl-3H-xanthen-9-yl], perchlorate
Rhodamin 590Rhodamine 590
Benzoic Acid, 2- [ 6- (ethylamino) -3- (ethylimino) -2 , 7-dimethyl-3H- xanthen-9-yl] -ethyl ester ,monohydrochlorideBenzoic acid, 2- [6- (ethylamino) -3- (ethylimino) -2, 7-dimethyl-3H-xanthene-9-yl] ethyl ester, monohydrochloride
Rhodamin 610Rhodamine 610
2- [ 6- (Diethylamino) -3- ( diethylimino ) -3H-xanthen-9-yl ] benzoic acid2- [6- (diethylamino) -3- (diethylimino) -3H-xanthene-9-yl] benzoic acid
Pyrromethene 546Pyrromethenes 546
1,3,5,7, 8-pentamethylpyrromethene-difluoroborate complex1,3,5,7,8-pentamethylpyrromethene difluoroborate complex
Pyrromethene 556Pyrromethenes 556
Disodium-1 ,3,5,7, 8-pentamethylpyrromethene-2 , 6-disulfonate- difluoroborate complexDisodium-1, 3,5,7, 8-pentamethylpyrromethene-2, 6-disulfonate-difluoroborate complex
Pyrromethene 567Pyrromethenes 567
1,3,5,7, 8-pentamethyl-2 , 6-diethylpyrromethene-difluoroborate complex1,3,5,7,8-pentamethyl-2, 6-diethylpyrromethene-difluoroborate complex
Pyrromethene 580Pyrromethenes 580
1,3,5,7, 8-pentamethyl-2 , 6-di-n-butylpyrromethene-difluoroborate complex1,3,5,7,8-pentamethyl-2, 6-di-n-butylpyrromethene-difluoroborate complex
Pyrromethene 597Pyrromethenes 597
1,3,5,7, 8-pentamethyl-2 , 6-di-t-butylpyrromethene-difluoroborate complex1,3,5,7,8-pentamethyl-2,6-di-t-butylpyrromethene-difluoroborate complex
Irgacure 184 1-Hydroxy-cyclohexyl-phenylketonIrgacure 184 1-hydroxy-cyclohexyl phenyl ketone
Irgacure 819 Bis-acylphosphinoxidIrgacure 819 bis-acylphosphine oxide
BYK 333 PolymethylalkylsiloxanBYK 333 polymethylalkylsiloxane
BYK 088 Mischung eines schaumzerstörenden Mineralöls und PolysiloxanBYK 088 Mixture of a foam-destroying mineral oil and polysiloxane
Ebecryl 111 aliphatisches MonoacrylatEbecryl 111 aliphatic monoacrylate
Ebecryl 112 aliphatisches Monoacrylat Ebecryl 284 difunktionales aliphatisches Polyurethanacrylat (Molgewicht 1200 g/mol) IRR 245 difunktionales aliphatisches Polyurethanacrylat (Molgewicht 6100 g/mol) P37 oligo eres BenzophenonEbecryl 112 aliphatic monoacrylate Ebecryl 284 difunctional aliphatic polyurethane acrylate (molecular weight 1200 g / mol) IRR 245 difunctional aliphatic polyurethane acrylate (molecular weight 6100 g / mol) P37 oligo eres benzophenone
Tinuvin 400Tinuvin 400
Figure imgf000009_0001
Figure imgf000009_0001
2-[2-Hydroxy-4-( 2-hydroxy-3-dodecyloxy-propyloxy)phenyl]-4 , 6- bis ( 2 , 4-dimethylphenyl ) 1,3, 5-triazin2- [2-Hydroxy-4- (2-hydroxy-3-dodecyloxypropyloxy) phenyl] -4, 6- bis (2,4-dimethylphenyl) 1,3,5-triazine
LD 466 7-Diethylaminocoumarin LD 466 7-diethylaminocoumarin

Claims

Patentansprüche : Claims:
1. Verfahren zur Herstellung eines transparenten Überzugsmittels für die Beschichtung von Holz, bei dem ein Bindemittel aus der Gruppe der physikalisch trocknenden Acrylatharze oder strahlenvernetzenden Acrylatharze ausgewählt und dann mit zumindest einem hocheffizienten und lichtstabilen Laserfarbstoff dotiert wird, der in Form von 0,1 - 5,0 Gew.-% bezogen auf die Gesamtzusammensetzung in dem Binde ittel- molekular dispers gelöst wird und den UV-Anteil des UV- Lichtes sowie spektrale Lichtanteile im Wellenlängenbereich zwischen 280 nm und 500 nm vollständig oder selektiv absorbiert und mit einer Konversionseffizienz von _> 30% in längerwellige, die Holzsubstrate und das Bindemittel nicht schädigende Strahlung umwandelt, wobei zumindest ein1. A process for producing a transparent coating for the coating of wood, in which a binder is selected from the group of physically drying acrylate resins or radiation-curing acrylate resins and then doped with at least one highly efficient and light-stable laser dye, which is in the form of 0.1-5 , 0% by weight based on the total composition in which binder is molecularly dispersed and completely or selectively absorbs the UV component of the UV light and spectral light components in the wavelength range between 280 nm and 500 nm and with a conversion efficiency of _> Converts 30% into longer-wave radiation that does not damage the wood substrates and the binding agent, whereby at least one
Photoinitiator, Hilfsstoffe und gegebenenfalls Lösemittel beigemischt werden.Photoinitiator, auxiliaries and optionally solvents are added.
2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, dass als Photoinitiator Methylbenzoylformat , Irgacure 184, Irgacure2. The method according to claim 1, characterized in that as photoinitiator methylbenzoyl format, Irgacure 184, Irgacure
819 oder P37 (Benzophenonderivat) allein oder in Kombination eingesetzt wird.819 or P37 (benzophenone derivative) is used alone or in combination.
3. Verfahren nach Anspruch 1 oder 2, dadurch gekennzeichnet, dass als Acrylatharze UV-vernetzende Polyurethanacrylate verwendet werden .3. The method according to claim 1 or 2, characterized in that UV-crosslinking polyurethane acrylates are used as acrylate resins.
4. Verfahren zur Herstellung eines transparenten Uberzugsmittels für die Beschichtung von Holz, bei dem ein Bindemittel aus der Gruppe mittel- bis langöliger Alkydharze auf Basis trocknender Fettsäuren und/oder trocknender Öle ausgewählt und dann mit zumindest einem hocheffizienten und lichtstabilen Laserfarbsto f dotiert wird, der in Form von 0,1 - 5,0 Gew.-% bezogen auf die Gesamtzusammensetzung in dem Bindemittel molekular dispers gelöst wird und den UV-Anteil des UV-Lichtes sowie spektrale Lichtanteile im Wellenlängenbereich zwischen 280 nm und 500 nm vollständig oder selektiv absorbiert und mit einer Konversionseffizienz von >. 30 % in längerwellige, die Holzsubstrate und das Bindemittel nicht schädigende Strahlung umwandelt, wobei Hilfsstoffe und gegebenenfalls Lösemittel beigemischt werden.4. A process for producing a transparent coating for the coating of wood, in which a binder is selected from the group of medium to long-oil alkyd resins based on drying fatty acids and / or drying oils and then doped with at least one highly efficient and light-stable laser dye, which in the form of 0.1 - 5.0 wt .-% based on the total composition in the Binder is molecularly dispersed and completely or selectively absorbed the UV component of the UV light and spectral light components in the wavelength range between 280 nm and 500 nm and with a conversion efficiency of> . 30% is converted into longer-wave radiation that does not damage the wood substrates and the binding agent, with additives and optionally solvents being added.
5. Verfahren nach einem der vorhergehenden Ansprüche, dadurch gekennzeichnet, dass der zumindest eine Laserfarbstoff auf den Anwendungszweck abgestimmt und aus speziellen Rhodaminen,5. The method according to any one of the preceding claims, characterized in that the at least one laser dye is matched to the application and made of special rhodamines,
Pyrromethenen, Exaliten, Furanen oder Lumogenen ausgewählt wird.Pyrromethenes, exalites, furans or lumogens is selected.
6. Verfahren nach einem der vorhergehenden Ansprüche, dadurch gekennzeichnet, dass der zumindest eine Laserfarbstoff in Kombination mit einem organischen UV-Absorber verwendet wird.6. The method according to any one of the preceding claims, characterized in that the at least one laser dye is used in combination with an organic UV absorber.
7. Verfahren nach einem der vorhergehenden Ansprüche, gekenn- zeichnet durch den Zuschlag von Füllstoffen. 7. The method according to any one of the preceding claims, characterized by the addition of fillers.
PCT/DE2000/003096 1999-09-09 2000-09-07 Method for producing a wood coating agent WO2001018131A1 (en)

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CN103937401A (en) * 2013-01-17 2014-07-23 合众（佛山）化工有限公司 Preparation method of scratch resistant double-component polyurethane woodenware glossy vanish
JP2014231592A (en) * 2013-04-30 2014-12-11 横浜ゴム株式会社 Uv-curable resin composition, and laminate using the same
WO2016002670A1 (en) * 2014-06-30 2016-01-07 横浜ゴム株式会社 Ultraviolet-curable resin composition and laminate using same
CN105505193A (en) * 2015-12-26 2016-04-20 上海巴德士化工新材料有限公司 Environment-friendly smell purifying PU white finish with good weather resistance and high edge covering performance, whiteness and gloss

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US6955167B2 (en) 2002-03-18 2005-10-18 Electrolux Professional Outdoor Products, Inc. Pavement working apparatus and methods of making
US7757684B2 (en) 2002-03-18 2010-07-20 Electrolux Professional Outdoor Products, Inc. Movable machinery, including pavement working apparatus and methods of making
JP6243368B2 (en) 2015-02-27 2017-12-06 ファナック株式会社 Adhesion method for adhering parts with energy ray curable adhesive

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Cited By (4)

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Publication number Priority date Publication date Assignee Title
CN103937401A (en) * 2013-01-17 2014-07-23 合众（佛山）化工有限公司 Preparation method of scratch resistant double-component polyurethane woodenware glossy vanish
JP2014231592A (en) * 2013-04-30 2014-12-11 横浜ゴム株式会社 Uv-curable resin composition, and laminate using the same
WO2016002670A1 (en) * 2014-06-30 2016-01-07 横浜ゴム株式会社 Ultraviolet-curable resin composition and laminate using same
CN105505193A (en) * 2015-12-26 2016-04-20 上海巴德士化工新材料有限公司 Environment-friendly smell purifying PU white finish with good weather resistance and high edge covering performance, whiteness and gloss

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